Water → 2-Amino-6-(2-furyl)pyrimidine-4-carboxylic acid

HRID 254153Notes

Reaction equation

HRID 254153 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]#N)[CH:5]=[C:4]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[N:3]=1.S(=O)(=O)(O)[OH:16].[OH2:20]>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:16])=[O:20])[CH:5]=[C:4]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[N:3]=1

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 668464412-Amino-6-(2-furyl)pyrimidine-4-carbonitrile

Product 1

HCID 287995992-Amino-6-(2-furyl)pyrimidine-4-carboxylic acidYield 90%

Conditions

Temperature
100 °C

Procedure

A suspension of 2-amino-6-(2-furyl)pyrimidine-4-carbonitrile (7.06 g, 37.9 mmol) in water (30 mL) was treated carefully with concentrated sulfuric acid (30 mL), stirred at 100° C. for 2 h, allowed to cool to room temperature and poured onto a mixture of ice (150 g) and water (150 mL). After standing for 1 h the crude product was filtered off, washed with water and MeCN, and dried in air to give the title compound (7.02 g, 90%) as a brown solid; NMR δH (400 MHz, DMSO) 6.71 (1H, dd, J 1.6, 3.6 Hz), 7.04 (2H, br s), 7.30 (1H, d, J 3.6 Hz), 7.36 (1H, s) and 7.94 (1H, d, J 1.2 Hz); Anal. Calc for C9H7N3O3.1.6H2O: C, 46.20; H, 4.39; N, 17.96. Found: C, 46.22; H, 4.22; N, 17.82.

Workup

  1. temperatureto cool to room temperature
  2. waitAfter standing for 1 h
  3. filtrationthe crude product was filtered off
  4. washwashed with water and MeCN
  5. customdried in air

Sources & evidence

ORD record
ord-ba5f0a96091a42c59fdbc4c10df183c4
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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